Hydrochloric Acid → 3-(3-Methyl-4-oxo-5H-2-oxa-1,5,7-triaza-cyclopenta[a]naphthalen-5-yl)-cyclohexanecarboxylic acid

HRID 1823296Notes

Reaction equation

HRID 1823296 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH2:9][CH:8]([N:12]2[C:21]3[C:16](=[CH:17][CH:18]=[N:19][CH:20]=3)[C:15]3=[N:22][O:23][C:24]([CH3:25])=[C:14]3[C:13]2=[O:26])[CH2:7]1)=[O:5])C.[OH-].[Na+].C(O)C.Cl>O.O1CCCC1>[CH3:25][C:24]1[O:23][N:22]=[C:15]2[C:16]3[C:21](=[CH:20][N:19]=[CH:18][CH:17]=3)[N:12]([CH:8]3[CH2:9][CH2:10][CH2:11][CH:6]([C:4]([OH:5])=[O:3])[CH2:7]3)[C:13](=[O:26])[C:14]=12

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 696526573-(3-Methyl-4-oxo-5h-2-oxa-1,5,7-triaza-cyclopenta[a]naphthalen-5-yl)-cyclohexanecarboxylic acid ethyl ester

Product 1

HCID 221701653-(3-Methyl-4-oxo-5H-2-oxa-1,5,7-triaza-cyclopenta[a]naphthalen-5-yl)-cyclohexanecarboxylic acidYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Combine 3-(3-methyl-4-oxo-5H-2-oxa-1,5,7-triaza-cyclopenta[a]naphthalen-5-yl)-cyclohexane-carboxylic acid ethyl ester (620 mg, 1.75 mmol) with aqueous sodium hydroxide (2N, 5.0 mL, 10.0 mmol), ethanol (2 mL), and tetrahydrofuran (2 mL) and stir at ambient temperature until hydrolysis is complete. Add water and adjust to approx. pH 3.0 with aqueous hydrochloric acid. Extract with dichloromethane and dry over sodium sulfate and concentrate in vacuo to give the desired acid as a tan solid (500 mg, 88%).

Workup

  1. extractionExtract with dichloromethane
  2. dry with materialdry over sodium sulfate
  3. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-dc98c1d5c540450194d37a1edb7af438
Source dataset
uspto-grants-2006_05
Patent number
US07037921B2

Reaction notes

Loading…